Great chop, but just personally I feel the cross-eyed and toothless look adds a cliche feel to it

Thanks. I guess you are not a MAD magazine fan are ya. Perhaps it is an American thing. Alfred E. Neumann is a timeless icon and about the highest form of Western satire as it gets. You may not like it but MAD fans will love it which is the target audience in this case.

Who could have thought that one day Barack Obama would be happily walking hand in hand with Kim Jong-Un? Well, folks, this day has finally come, according to the today's stock photo. Have at it!
Photoshop this photo of President Obama and Kim Jong-Un impersonators any way you wish.

Today's stock photo comes from the White House Press Service archives. It's a personal favorite photo of President Obama from 2012, and shows him pretending to be caught in the kid Spider-Man's web.
Photoshop this photo of Obama and a Spider-Man kid any way you wish.

This Saturday we continue our freaking experiment with provided source images. After the recent tensions over Snowden, and then Syria, the foreign affairs between the US and Russia has hit the new low and descended into the state of mistrust and cold treatment. Are we heading to a new cold war?
Photoshop this image of Obama and Putin any way you wish. Some examples are - turn this "state of confusion" into a happy affair between the presidents, use the photo in billboards and promotional posters. These are just some ideas.

This Saturday we continue our freaking experiment with provided source images.
Photoshop this image of Obama and Putin at the G20 Summit in St.Petersburg, Russia, on September 6, 2013 any way you wish. Some examples are - show how things could go wrong between Obama and Putin on this summit, use the presidents in propaganda posters and movies, demotivational posters. These are just some ideas.

This Friday we continue our freaking experiment with provided source images.
Photoshop this image of President Obama on a Friday walk any way you wish (image credit Pete Souza / US Government work). Some examples are - showing where Obama is heading, designing a poster with this Obama walking image, putting the president into some new environment, movies, paintings, etc. These are just some ideas.